


New Year's Dean

by Wayward_and_Worn



Series: Life With Dean [1]
Category: Supernatural
Genre: F/M
Language: English
Status: Completed
Published: 2019-12-29
Updated: 2019-12-29
Packaged: 2021-02-27 04:28:14
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,462
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22011070
Author URL: https://archiveofourown.org/users/Wayward_and_Worn/pseuds/Wayward_and_Worn
Summary: Sam is gone.  Sacrificing himself for the greater good and is in the Cage.  Dean deciding to try the normal life.  Lisa does not exist here.
Relationships: Dean & Reader, Dean & You, Dean Winchester & Reader, Dean Winchester x Reader, Dean Winchester/You
Series: Life With Dean [1]
Series URL: https://archiveofourown.org/series/1633741
Comments: 12
Kudos: 68





	New Year's Dean

In early November, she discovered a new neighbor. The apartment just across the entryway from hers had been vacant for at least a year. As she was returning home from work one day, coming out of the garage stairwell, she noticed the man carrying a few bags into the now open door of the apartment. In speaking to him briefly, she learned that his name was Dean, he had amazingly green eyes, he wasn’t from around here, he drove a fantastic classic car, and finally, he was fond of flannel. The last part she figured out by noticing that the bag in his hands had at least 5 different patterns. 

“Moving at this time of year…” she began with a grin.

“Is a terrible idea, I know.” He tossed the bag through the door and rubbed at the back of his neck. Grinning. “Fortunately, I travel light. Everything fits in the car.”

“No furniture?”

“Not yet.”

“You’re just sleeping on the floor?”

“Hey, it’s not as bad as it sounds. I’ve slept in far worse. It’s warm. It’s dry.” He shrugged, “I gotta find work first. Then furniture.”

Common sense told her that he probably wanted this particular conversation to be over, but she wasn’t quite done. “You have blankets and stuff, right?”

Again, neck rub and this time he glanced down at his boots. 

“I have tons of blankets and pillows. Will you accept some? Just for now. Just until you’re more settled?” She tried to smile reassuringly. “I promise that I’m not that nosey motherly neighbor. I’m just a HUGE champion of comfy sleeping spaces.” 

He shrugged again, his grin never fading, “Why not.”

In less than five minutes, she was back through the door with a camping cot, pillows and blankets. 

“Jesus!” he exclaimed, rushing to take the handles of the cot case as she headed in the direction of his door. “You didn’t say you were going to come out here with a freaking bed.”

“There,” she said with satisfaction, dropping the soft pile inside the door. “Now I’ll sleep better.”

“Judging by this, I certainly will too. Thank you.” He winked and her stomach did a weird flip, “Thank you so much.”

“You’re welcome. You can keep this stuff for as long as you need. Like I said, I have plenty.” She smiled and returned to her apartment. 

That night, as Dean settled on the cot; piled high with ALL the blankets and pillows, he sighed happily. He hadn’t been on something so soft in quite a while. His thoughts drifted to the generous girl with the pretty eyes across the way. The smell of fabric softener and the unique scent of her home filled his senses as he fell into a deep sleep. 

He woke up the next morning, momentarily confused at the softness around him. Yawning, he rubbed at his eyes, remembering the day before. A soft slam in the distance told Dean she had either just left or arrived. Probably working, he thought.

Work. Right. 

Scrolling through ads on his phone while coffee brewed, he found an ad for a place right by the complex. Close enough to walk; saving gas for Baby until…

Until what?

He sighed heavily. He didn’t know what the hell he was doing. But he needed money. He showered, dressed, and headed out hoping that his REAL social security number wouldn’t land him in prison. 

She didn’t see Dean for a couple of weeks. Noticing that his car didn’t move too often. She didn’t see lights on in the apartment very often either. She had been debating just going and knocking on his door, just to make sure he wasn’t dead in an empty room. Eventually though, she did see him walking up the complex driveway into their lot. “Car broken?” She called.

He looked up, his eyes lighting up when they landed on her. He smiled, “Oh, hey you. No, I got a job at the garage right up on the corner here. No need to drive unless the weather is total shit.”

“Oh, that’s great!” She smiled, “That is great, right?” She looked up at him. He really was tall. 

He laughed lightly, “Yeah, it’s a start. And tomorrow is my first payday. I’m really looking forward to McDonalds over ramen.” He raised his hand before she could reply, “And! I’m going to go get some stuff. I got this neighbor that insists that I need things. Like, lamps.”

She squinted at the handsome man. “Stupid nosy neighbors.” 

He stuffed his hands in his pockets. “Eh, she’s really been nice to me so I can’t complain.”

She laughed, was he blushing? Was SHE blushing? “Well okay then.”

A few weeks later:

The door at the top of the stairwell flew open just as she reached for the knob. “Woah!” 

“Oh, sorry,” Dean replied with widened eyes and a smile. “Come on up.”

She smiled and stepped around him, her arms full of grocery bags. She was just returning from the store, again, in preparations for her annual New Year’s Eve party that evening. “Thanks Dean,” she said as she passed behind him, expecting him to disappear through the door she’d just come through down to the garage. 

“Of course,” he turned, still holding the door open, but giving her his attention.

“How are you doing? Get those lamps yet?”

His tongue peeked out to swipe along his bottom lip, “Two of ‘em. But man, stuff is expensive.” 

“Yeah, it really is. Especially if you don’t want to build anything.” She turned back to fumble at the key in the lock when she started losing control of her bags. “Waaa…”

“Uh oh!” Dean lurched forward, grabbing the escaping bag out of her arms before it headed for the pavement. Peeking in the bag, he grinned, “Can’t have the whiskey break.”

“Oh god no.” Finally getting the key in the door and swinging it inside. She stepped in, placing the bags on the table just inside. “I’ve already been to the store 3 times. I’m having a hell of a time today, for some reason.”

Handing her the bag, he nodded, “I know those days.”

“So now that I have—” she blanched. “Oh shit.”

“What did you forget?”

“Butter.” She sighed heavily and reached to pull the door closed behind her, “Dammit,” she cursed.

“Hey hey, look, I was just headed out to the store myself, I am coming right back, I’ll grab it for you if you like.”

“Really?”

“Yeah, we’re neighbors, and you’re still the first one I’ve met so far.” He smiled again. “What kind?”

She told him and reached in her pocket for cash when he waved her off and headed back towards the door to the garage. “Pay me when I get back.”

But when he returned with her butter, he refused her money. “Please. It’s the least I can do.” 

“But…” she looked down at the other bag in his hand. “Pizza and chocolate milk?”

He nodded, glancing down at the bag, “New Year’s extravaganza. It’s a great combination, you should try it.”

“No parties, or plans?” She wasn’t sure if the plan forming in her mind was a good one, but she was going to roll with it. 

He shook his head, “Nah, I don’t have a lot of…connections. Pizza, chocolate milk, horror marathon and I’m good to go.” He smiled. “Don’t worry, I’m good.”

“Well, my party starts around 7. You’re more than welcome to come.” A thought occurred to her, “I will have a TON of food. Usually a ton of leftovers.”

He opened his mouth, then paused, “I do like food.” He thought a moment, tilting his head adorably back and forth, “Thanks, maybe I’ll take you up on that.”

She tried not to spend too much time hoping the handsome neighbor would show up. As her guests arrived, all couples, she swallowed back the sadness and loneliness that always came with the territory. However, as usual, once the party was going, those feelings dimmed. 

The doorbell startled everyone a little after 9. 

Rushing to open it, she was genuinely surprised and, not to mention, pleased to see Dean. He’d changed. Jeans and boots, but instead of a flannel, he had a dark red Henley. “Come on in!”

She took Dean around the room, introducing him to her friends, making sure to skitter away before 20 questions could start. She was mostly successful until her closest friend literally cornered her by the bathroom. 

“WHERE did he come from? And holy SHIT is he good looking.”

“If he hears you Em, I swear to god I’m breaking your legs.”

“Well I guess that answers my question as to whether you like him or not,” she snickered. “He’s REALLY nice, too.”

“I know.” She shoved lightly at her friend, “Now fuck off, I have to get in here.” 

As midnight approached, Dean noticed Y/N getting a little fidgety. Just before the countdown started, he saw her slipping out onto her patio. Quickly detangling from a terribly boring conversation about accounting, he followed her. 

“What are you doing out here?” Dean asked as he found her at the railing, gazing towards the parking lot. 

“I always come out her for the ball drop.”

“Why?”

“No one to kiss. And, to be honest, I’m tired of watching everyone else. So, I come out here.” She nodded towards the apartment. “They all know, so they leave me alone until after.”

“So you host the annual party, but you don’t even get…”

She shrugged, “It’s the way it is. This way I get to see all my friends and we all know that we’ll all be alive in the morning.” She laughed sadly, “It’s the way it is.” 

Inside, the merrymakers began shouting. “Ten!” Dean watched her tilt her head towards the sound. 

“Allow me to be you New Year’s kiss stand-in.” He turned his whole body to face her, gently reaching out to place his hand at the back of her neck. She turned, letting him guide her to face him. “Please?” 

“Five!...”

His arm wrapped around her waist, pulling her against his strong body, she met Dean’s eyes. A deep forest green in the dim lights. “May I?”

She nodded.

“Two!...One!!!”

He placed his other hand on her cheek and pressed his lips to hers. The soft, sweet kiss quickly increased in pressure as she wrapped her arms around his waist and his hand pushed up into her hair, cradling the back of her head. 

Tilting her head to the side, she opened her mouth, shivering a bit when Dean moved as well. The soft touch of his tongue against her lip had her opening her mouth to accept. A soft whimper from her, and a growl from him as he crushed her to him.

When they pulled back, they were panting slightly. “Happy New Year,” he scanned her face expectantly. 

“Happy New Year indeed,” she replied, feeling warm and dazed. 

“No need for it to stop,” Dean leaned back in when her patio door opened and Em stuck her head out, “Alright cowards, get in here! You’ll freeze to death!”

“I am perfectly warm,” Dean said quietly as she took his hand to lead him back inside.

They hovered near each other for the rest of the evening. When the party started to wind down, she tried not to shove everyone out the door. She hoped that Dean wanted to stay. Once the last guest was hugged and wished well, Dean spoke. “Do I have to go too?”

She smirked, “Well, the party IS over. Unless you’re going to help me clean?”

“Well, there are other things that we could do.” He stood, “I liked what we started out on the patio earlier.”

“Oh? Gosh, I wouldn’t want you to think that I’m easy.”

She smiled as she watched him come up with his next reply. With a grin, and an adorable sparkle, he replied, “Well I don’t have a bed. You’d put me out in this cold? Bedless?”

“One, your door is right there.” She pointed towards the doorway with a laugh. “And B, you DO have a bed. Sort of.”

“I’ve had a few beers. I’m not used to the area. I might get lost.” He attempted puppy dog eyes while he crossed the room towards her. “How would you like that on your conscience?” 

“In that case, can you make me cum so hard that the neighbors will know your name?” She replied.

“I—what?” Shocked at the sudden shift, his thought train completely derailed. He looked down at her, his eyes filling with want. 

“You want to stay. I want you to stay. But if I’m going to share BOTH of my beds with you, I’m making sure that it’s worth my while.”

He pulled her into his arms, his arousal obvious. “I—yes. Yes, I can do that. I won’t disappoint you.” This time, when their lips met, his tongue was hot and urgent against her own. He walked backwards, guiding her into the bedroom, only stopping when the back of his knees hit the mattress and he fell/sat. Burying his face in her stomach, he breathed in deep, while running his hands around to squeeze her ass.

“All my bravado aside,” she began, running her hands through his spiky tufts. “I haven’t done this in a while. So I’m gonna be kind of rusty.”

Pulling his head back and resting his chin on her stomach, he looked up at her in adoration. “I am not concerned about that at all. You want me to make you cum hard. And I’m gonna do that.” He began working at her jeans, while she pulled her top up over her head. “You don’t have to do a thing.”

She ran her fingertips down his cheek and across his jaw. “Well I would like to do SOME things.” She bent down for a kiss, allowing him to stand, turn and guide her to sit on the edge of her bed. Once there, he knelt before her, pulling off her shoes and jeans, leaving her completely bare. 

He leaned in, his lips against her neck, whispering, “Lay back.”

She obeyed. 

He spent a very long time working his way from the inside of her knee, up her thigh and almost to her core before he started back down the other thigh. She could feel herself getting wet as she felt his soft lips and breath caressing her skin. She moaned when she felt his hand cover her mound, pressing gently. She moved her hips towards him, and he slipped a finger between her folds, gently brushing past her clit. She swore that she heard him purr. 

“Dean,” she said softly. 

“Hmm?” he rose up on his knees, running both hands up her stomach to cover both of her breasts in his large hands. Squeezing gently while he pressed his hips against her core. The roughness of his jeans along the inside of her thighs made her shiver. “I take it you want more?”

She arched up into his hands. “Yes.”

Without another word, he kissed his way from her stomach down to her thighs again. She thought, for a moment, that he would continue teasing her again. Instead, he parted her folds and pressed his tongue to her clit. The wet heat of his mouth causing her to involuntarily gasp and jerk her hips towards his mouth. 

From there, Dean devoured her. Using his lips, tongue and fingers to pleasure her so quickly, she found herself trying to take a handful of his hair to keep him still. “There, right there!” She choked out. “Ohgoddon’tstop.”

Dean growled, pushing himself forward and increasing the pressure on her, causing her orgasm to crest and wash her away. Writhing beneath him, she moaned and cried out as she rode the waves. 

When he pulled away, she lay there panting for a moment before raising her head. Before her, standing between her knees was Dean, flushed and looking very pleased with himself. “More?” He challenged. 

She sat up, reaching for his belt and tugging at it with purpose. “More.” She demanded, yanking the leather free and working at the button. She then pulled his jeans and boxers down, freeing the impressive erection. She couldn’t help but raise her eyebrows as it bobbed happily. Immediately wrapping her hand around the base, she dragged her tongue over the head. She was rewarded with a hiss and his hand on her shoulder. 

“Oh,” Dean managed before she covered the head with her mouth. His head fell back, and he pushed his hips forward, sliding further into her mouth. “Fuuuck.” After pulling off his own shirt, he looked down his body to see her bright eyes staring up at him. He almost lost it right then. “You don’t seem rusty to me,” he gasped. 

She hummed a laugh that earned a whole new growl from him and he plunged his hands into her hair. She liked that. She encouraged him by grabbing handfuls of his ass and pulling his cock fully into her mouth. He shouted briefly and began thrusting in and out. 

But soon, he pulled back with a pained moan. His cock popping out of her mouth with a comical sound. He leaned down to capture her mouth in a hard kiss. “More.” He whispered, guiding her fully onto the bed, resting her head on the pillows. “I want to see your eyes when you cum.”

She let him move her, reaching for him when he settled between her legs, his cock nudging urgently at her entrance. She looked down to where they were about to join but he took a hand and tipped her chin up. His eyes widened as he sheathed himself inside her, watching her eyes almost roll back in her head as she felt him fill her up. “Hard,” she said, putting her hands at his waist and urging him forward. “Please…do me hard.”

He slid almost completely out then slammed back into her. She shifted up the bed with the force and his name burst from her lips. Followed by, “Yes! Just like that.”

Dean obliged, slamming his hips into hers, her legs falling open to accommodate his thrusts. He wasn’t going to last long like this, so he rose up on his knees, pulling her to drape over his lap so he could massage her clit while still seeing her face. He was fascinated with the pleasure on her face as he penetrated her. Her cries and moans causing him to throb even as he moved. 

He felt his insides tighten just as she started to tremble. He tried to keep his hand steady as his rhythm began to stutter. “Look at me,” he growled down at her. When her eyes popped open and met his, he was lost and liquid fire exploded from his center, pulsing into her at the same time she began to convulse and jerk her hips against him. 

When the largest waves had passed, he collapsed against her, rolling right away and taking her with him, trying not to slip out just yet. She accommodated by throwing her leg over the outside of his hip. Panting, he pushed her hair away from her face. “More?” He breathed. 

She chuckled, the vibrations tickling his over sensitive cock where it still rested within her. “Enough.” She leaned in for a kiss. “For now.”  


They dozed.

“I don’t know about you,” his voice was warm and soft at her ear, “But I think this is a hell of a start to the new year.” They had shifted, and now Dean was the big spoon, holding her warm body against his. God, it felt good to be in a bed, with a woman. His cock started to stir. 

She stretched as she came awake, making sure to arch and press her bottom against him. Her yawn was swallowed by her smile as he grunted softly and gripped her hip in his large, warm hand. 

“You’re doing that on purpose.” He accused, pressing fully against her back. His cock now fully erect and ready. 

“Yes I am.” She reached back, running her hand over his thigh. “Hoping to entice you into another round.”

He pushed her onto her back, leaning over her and claiming her lips in a fiery kiss. “If the answer to that question is ever “no”—“ his voice trailing off as his eyes roamed her body. He moved his hips to notch himself at her entrance again. He then snapped his attention back to her eyes. “I’m pretty sure that I have enough rounds in me to get us through to next year.” 

**Author's Note:**

> I thought about calling this “New Years D” but, while accurate, I just couldn’t bring myself to do it.


End file.
